Organic Compounds in Produced Waters from. Shale Gas Wells
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- Britney Hunt
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1 Electronic Supplementary Material (ESI) for Environmental Science: Processes & Impacts. This journal is The Royal Society of Chemistry 2014 Organic Compounds in Produced Waters from Shale Gas Wells Samuel J. Maguire-Boyle and Andrew R. Barron * Department of Chemistry, Rice University, Houston, Texas 77005, USA Department of Materials Science and Nanoengineering, Rice University, Houston, Texas 77005, USA College of Engineering, Swansea University, Singleton Park, Swansea, SA2 8PP, Wales, UK Electronic Supplementary Information
2 Figure S1. Plot of ph of produced water as a function of the calcium concentration (R 2 = 0.964).
3 Figure S2. Plot of total cation content as a function of produced water conductivity (R 2 = 1.00).
4 Table S1. List of wavelengths of analyzed elemental ions for ICP-OES. Element Wavelength (nm) a Na K , Li , , , Cs , Rb , Mg , , , Ca , , , , Sr , , Ba , , , , Sc , , Y , , La , , , Ti , , , , V , , , , , Cr , , , , , , Mn , , , , , , Fe , , , , , Ni , , , , Cu , , , , , Zn 206.2, , , Cd , , , Hg , , , , , , B , , , , , Si , , , , Sn , , ,
5 P , , , , As , , , Sb , , , , , Bi , , , S , , , a Where more than one wavelength is given they are listed in the order they are ranked (most to least confident).
6 Table S2. List of identified molecules with GC-MS from Marcellus (PA) neutral aliquot extracted with chloroform. Peak R.T. A[tot] Library/compound ID Q CAS # M w Molecular formula (min) (%) (%) Propanone C 3 H 6 O Trichloromethane CHCl Methylcyclohexane C 7 H Methylheptane C 8 H Methylbenzene C 7 H ,3-Dimethylcyclohexane C 8 H ,1-Dimethylcyclohexane C 8 H Octane C 8 H ,3-Dimethylcyclohexane C 8 H ,4-Dimethylheptane C 9 H ,6-Dimethylheptane, C 9 H Ethylcyclohexane C 8 H ,2,4-Trimethylcyclohexane C 9 H Methyloctane C 9 H Methyloctane C 9 H ,3-Dimethylbenzene C 8 H 10
7 ,1,3,5-Tetramethylcyclohexane C 10 H Ethyl-4-methylcyclohexane C 9 H Nonane C 9 H Chloro-5-(chloromethoxy)-pentane C 6 H 12 C l2 O Ethyl-4-methyl-cyclohexane C 9 H ,4-Dimethylhexane C 8 H Hexyne C 6 H ,5-Dimethyloctane C 10 H ,6-Dimethyloctane C 10 H ,6-Dimethyloctane C 10 H ,2-Dimethylcycloheptene C 9 H ,3,5,5-Tetramethylcyclopentane C 9 H Ethyloctane C 10 H Methylnonane C 10 H Methylnonane C 10 H ,2,3-Trimethylbenzene C 9 H Methyl-2-propylcyclohexane C 10 H Decane C 10 H ,2-Dimethyl-3-(1-methylethyl)-cyclopentane C 10 H 20
8 ,7-Dimethylundecane C 13 H Methyldecane C 11 H Methyldecane C 11 H Butylcyclohexane C 10 H Methyldecane C 11 H Methyldecane C 11 H Methyldecane C 11 H Methyldecane C 11 H Methyldecane C 11 H ,2,4,5-Tetramethylbenzene C 10 H Ethyl-1,2-dimethylbenzene C 10 H ,1,3-Trimethylcyclopentane C 8 H Undecane C 11 H (1-Methylbutyl)-benzene C 11 H Decahydro-2-methylnaphthalene C 11 H Dodecane C 12 H ,2,4,5-Tetramethylbenzene C 10 H Methylundecane C 12 H Pentylcyclohexane C 11 H 22
9 Tritetracontane C 43 H Methyldecane C 11 H Methyl-4-(1-methylpropyl)-benzene C 11 H ,6-Dimethyldecane C 12 H Methylundecane C 12 H Methylundecane C 12 H Methyldecane C 11 H (1α, 3β, 4α, 5α, 7β)-1,4-Dimethyl C 12 H 20 tricyclo[ ]decane (1α, 3β, 4β, 5α, 7β)- 1,4-Dimethyl C 12 H 20 tricyclo[ ]decane Methyl-2-pentylcyclohexane C 12 H Methylene-1H-indene C 10 H Dodecane C 12 H C 12 H (1α, 3β, 4α, 5α, 7β)-1,4-dimethyltricyclo[ ]decane ,6-Dimethylundecane C 13 H ,1'-Oxybisdecane C 20 H 42 O Chlorohexadecane C 16 H 33 Cl
10 Hexatriacontane C 36 H Hexylcyclohexane C 12 H ,4-Dimethylundecane C 13 H ,3-Dimethylundecane C 13 H Methyldodecane C 13 H ,6-Dimethyldodecane C 14 H ,6,11-Trimethyldodecane C 15 H Tridecane C 13 H Iodo-2-methylundecane C 12 H 25 I ,5-Dimethyldodecane C 14 H Cyclohexylbenzene C 12 H Heptylcyclohexane C 13 H Methyltridecane C 14 H Methyltridecane C 14 H Methyltridecane C 14 H Methyltetradecane C 15 H ,6,10-Trimethyldodecane C 15 H Tetradecane C 14 H ,9-Dimethylundecane C 13 H 28
11 α-(2-methylpropylidene)-benzeneacetaldehyde C 12 H 14 O Undecane C 11 H Methylpentadecane C 16 H Pentatriacontane C 35 H Pentadecane C 15 H ,7,11-Trimethyl-1,3,6,10-dodecatetraene C 15 H Tridecene C 13 H Methylpentadecane C 16 H Hexadecane C 16 H Methyldecane C 11 H Heptadecane C 27 H ,6,10,14-Tetramethylpentadecane C 19 H Octadecane C 18 H Nonadecane C 19 H Eicosane C 20 H Heneicosane C 21 H Docosane C 22 H ,6-Dioctyloatehexanedioic acid C 22 H 42 O 4
12 Table S3. List of identified molecules with GC-MS from Marcellus (PA) acid aliquot extracted with chloroform. Peak R.T. A[Tot] Library/ID Q CAS # M w Molecular Formula (min) (%) (%) Hydroxyacetic acid C 2 H 4 O Hydrazine N 2 H Chloroethanol C 2 H 5 ClO Methyl-1-butene C 5 H ,1-Dimethylcyclopropane C 5 H Methyl-2-butene C 5 H Methylpentane C 6 H Hexane C 6 H Trichloromethane CHCl Trichloromethane CHCl ,3-Dimethylcyclopentane C 7 H Heptane C 7 H Methylcyclohexane C 7 H Ethylcyclopentane C 7 H ,2,4-Trimethylcyclopentane C 8 H ,2,3-Trimethylcyclopentane C 8 H 16
13 Methyl-1-heptene C 8 H Methylheptane C 8 H Methylbenzene C 7 H ,3-Dimethylcyclohexane C 8 H Ethyl-2-methylcyclopentane C 8 H Octane C 8 H ,4-Dimethylheptane C 9 H ,6-Dimethylheptane C 9 H ,2-Dimethylcyclohexane C 8 H Ethylcyclohexane C 8 H ,1,3-Trimethylcyclohexane C 9 H Ethyl-2-methylcyclohexane C 10 H Methylenecyclohexane C 7 H ,2,4-Trimethylcyclohexane C 9 H ,3,5-Trimethylcyclohexane C 9 H ,3-Dimethylheptane C 9 H Ethylhexane C 8 H Octene C 8 H ,4-Dimethylheptane C 9 H 20
14 Ethylbenzene C 8 H Methyloctane C 9 H ,2,4-Trimethylcyclohexane C 9 H β-methylcyclopentanepropanol C 9 H 18 O Ethyl-4-methylcyclohexane C 9 H Ethyl-3-methylcyclohexane C 9 H Ethyl-3-methylcyclohexane C 9 H Nonane C 9 H ,1,3,5-Tetramethylcyclohexane C 10 H Ethyl-4-methylcyclohexane C 9 H Ethyl-2-methylcyclohexane C 10 H Cyclohexanepropanol C 9 H 18 O Propylcyclohexane C 9 H ,6-Dimethyloctane C 10 H Methylnonane C 10 H Methyl-3-hexene C 7 H Ethyl-2-methylheptane C 10 H (E)-3-Heptene C 7 H Ethyl-2,3-dimethyl-2-hexene C 10 H 20
15 (E)-5-Decene C 10 H (E)-5-Decene C 10 H Propylbenzene C 9 H Methylnonane C 10 H Nonene C 9 H Ethyl-3-methylbenzene C 9 H Methylnonane C 10 H ,2,4-Trimethylbenzene C 9 H Propylcyclohexanone C 9 H 16 O Propyl-3-heptene C 10 H Nonene C 9 H (2-Methylpropyl)-benzene C 10 H Methyldecane C 11 H Ethyl-3-methylbenzene C 9 H Propylcyclopentane C 8 H Ethyl-1,1,3-trimethylcyclohexane C 11 H (R)-3,7-dimethyl-6-octenal C 10 H 18 O Tridecyloate-2,2,3,3,4,4,4-heptafluorobutanoic C 17 H 27 F 7 O 2 acid
16 Pentatriacontene C 35 H Methyl-3-propylbenzene C 10 H Methyldecane C 11 H Methyldecane C 11 H Methyldecane C 11 H Methyldecane C 11 H Ethyl-2,4-dimethylbenzene C 10 H Undecane C 11 H Decahydro-2-methylnaphthalene C 11 H Decahydro-2-methylnaphthalene C 11 H Methyl-4-(1-methylpropyl)-benzene C 11 H ,2,4,5-Tetramethylbenzene C 10 H ,7-Dimethyldecane C 12 H Methylundecane C 12 H Methylundecane C 12 H ,2,4,5-Tetramethylbenzene C 10 H Ethyl-2,3-dimethylbenzene C 10 H Methylundecane C 12 H Methylundecane C 12 H 26
17 Dodecane C 12 H (1-methyl-1-buten-1-yl)-benzene C 11 H Dioctadecyloate phosphoric acid C 36 H 75 O 4 P ,6-Dimethylundecane C 13 H methyl-3-(1-methylethyl)-benzene C 10 H Pentyl-2-propylcyclopentane C 13 H ,6-Dimethylundecane C 13 H Methyldodecane C 13 H ,10-Dimethylundecane C 13 H Tridecane C 13 H Methyltridecane C 14 H (R)-3,7-Dimethyl-6-octenal C 10 H 18 O Tridecane C 13 H Methylnaphthalene C 11 H ,4-Dihydro-1,4-methanonaphthalene C 11 H (2-Buten-1-yl)-1,3,5-trimethylbenzene C 13 H Methyl-3-undecene C 12 H ,2,3,4-Tetrahydro-2,5,7-trimethylnaphthalene C 13 H Methyltridecane C 14 H 30
18 Methyloctane C 9 H ,6,10-Trimethyldodecane C 15 H ,7-Dimethylnonane C 11 H ,2,3,4-Tetrahydro-2,5,8-trimethylnaphthalene C 13 H Tetradecane C 14 H Dioctadecyloate phosphoric acid C 36 H 75 O 4 P ,5-Dimethylnaphthalene C 12 H ,7-Dimethylnaphthalene C 12 H ,3-Dimethylnaphthalene C 12 H ,6-Dimethylnaphthalene C 12 H ,7-Dimethylnaphthalene C 12 H ,5-Dimethylnaphthalene C 12 H ,6-Dimethylnaphthalene C 12 H ,7-Dimethylnaphthalene C 12 H ,7-Dimethylnaphthalene C 12 H Hexacosane C 26 H Pentacosane C 25 H Heptacosane C 27 H Hexadecene C 16 H 32
19 Pentadecane C 15 H Tritetracontane C 43 H Cyclopentadecane C 15 H Tetracontane C 40 H Methylnonadecane C 20 H ,3,6-Trimethylnaphthalene C 13 H ,6,7-Trimethylnaphthalene C 13 H Hexadecane C 16 H Tridecane C 13 H ,6,7-Trimethylcyclopentane C 8 H ,6,7-Trimethylnaphthalene C 14 H ,6,10-Trimethylpentadecane C 18 H Tridecane C 13 H Dodecane C 12 H ,1,3-Trimethylcyclopentane C 8 H ,6,10-Trimethyl-9-undecenal C 14 H 26 O Octadecene C 18 H (1-Pentyloctyl)-cyclohexane C 19 H Butyl-2-pentylcyclopentane C 14 H 28
20 Heptadecane C 27 H ,6,10,14-Tetramethylpentadecane C 19 H Heptadecene C 17 H Pentyl-2-propylcyclopentane C 13 H ,1,3-Trimethylcyclopentane C 8 H Tetradecane C 14 H Butyl-2-pentylcyclopentane C 14 H ,7,11-Trimethyl-2,6,10-dodecatrien-1-ol C 15 H 26 O ,7-Dimethyl-7-octenal C 10 H 18 O Octadecane C 18 H ,6,10,14-Tetramethylhexadecane C 20 H Butyl-6-hexyloctahydro-1H-indene C 19 H Cyclotetradecane C 14 H Pentyl-2-nonenal C 14 H 26 O Methyloate-2-butenoic acid C 5 H 8 O Nonadecane C 19 H Pentatriacontene C 35 H Methylphenanthrene C 15 H Methylanthracene C 15 H 12
21 a, 9b-Dihydro-1H-cyclopropa[1]phenanthrene C 15 H Methyl-4-tetradecene C 15 H Tetradecen-1-ol C 14 H 28 O ,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ol C 15 H 14 O Hexadecane C 16 H Bromo-1-tetradecene C 14 H 27 Br Eicosane C 20 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane (1,5-dimethylhexyl)-4-(4-methylpentyl) C 20 H 40 cyclohexane acetate-13-tetradecen-1-ol C 16 H 30 O Methylcyclopentadecanone C 16 H 30 O Tricyclo[ ]hexadeca-1,3,5,7,9,11, C 16 H 14 heptaene Octadecane C 18 H Octadecanethiol C 18 H 38 S Eicosane C 20 H Heneicosane C 21 H 44
22 acetate-8-methyl-9-tetradecen-1-ol C 17 H 32 O ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane ,2-Diethylcyclohexadecane C 20 H Chlorooctadecane C 18 H 37 Cl Eicosane C 20 H Docosane C 22 H Eicosane C 20 H Nonadecane C 19 H (Acetyloxy)-1,2,3-tributyloate-1,2, C 20 H 34 O 8 propanetricarboxylic acid ,2,3-Tributyloate-2-hydroxy-1,2, C 18 H 32 O 7 propanetricarboxylic acid Tricosane C 23 H Hexatriacontane C 36 H Methylnonadecane C 20 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane ,6,10-Trimethyl-9-undecenoic acid C 14 H 26 O 2
23 Tetracosane C 24 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane Tetracosane C 24 H Nonadecane C 19 H ,2-Diethylcyclohexadecane C 20 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane ,7,11-trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane, ,7,11-trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane Tetradecyloxirane C 16 H 32 O Tricosane C 23 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane Tetracosane C 24 H 50
24 ,2-bis(2-Ethylhexyl)oate-1, C 24 H 38 O 4 benzenedicarboxylic acid Hexacosane C 26 H Tricosane C 23 H (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-binaphthalene]-5,5',8,8'-tetrone '-Dodecyl-1,1':3',1''-tercyclopentane C 27 H Pentacosane C 25 H Octadecene C 18 H (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-Binaphthalene]-5,5',8,8'-tetrone Pentacosane C 25 H Hexacosane C 26 H Heptacosane C 27 H (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-Binaphthalene]-5,5',8,8'-Tetrone ,3-bis(2-ethylhexyl)oate-1, C 24 H 38 O 4 benzenedicarboxylic acid ,2-Dioctyloate-1,2-benzenedicarboxylic acid C 24 H 38 O 4
25 ,2-Diisodecyloate-1,2-benzenedicarboxylic C 28 H 46 O 4 acid Hexacosene C 26 H Tricosene C 23 H Pentacosane C 25 H Hexacosane C 26 H Tetracosane C 24 H Hexacosane C 26 H Hexacosane C 26 H Heptacosane C 27 H Butyl-2-(8-methylnonyl)-oate-1, C 22 H 34 O 4 benzenedicarboxylic acid Octacosane C 28 H ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O ,2-Diisodecyloate-1,2-benzenedicarboxylic C 28 H 46 O 4 acid ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O ,2-bis(8-Methylnonyl)oate-1, C 28 H 46 O 4 benzenedicarboxylic acid
26 ,2-Diisodecyloate-1,2-benzenedicarboxylic C 28 H 46 O 4 acid ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O ,2-bis(8-Methylnonyl)oate-1, C 28 H 46 O 4 benzenedicarboxylic acid ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O ,2-bis(8-Methylnonyl)-oate-1, C 28 H 46 O 4 benzenedicarboxylic acid Butyl-2-(8-methylnonyl)-oate-1, C 22 H 34 O 4 benzenedicarboxylic acid ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O ,2-bis(8-Methylnonyl)oate-1, C 28 H 46 O 4 benzenedicarboxylic acid ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O Butyl-2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid ,2-Diisodecyloate-1,2-benzenedicarboxylic C 28 H 46 O 4 acid
27 Butyl-2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid Butyl-2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid Hexacosane C 26 H Cyclotriacontane C 30 H (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-Binaphthalene]-5,5',8,8'-tetrone ,54-Dibromotetrapentacontane C 54 H 108 Br ,54-Dibromotetrapentacontane C 54 H 108 Br Bromo-11-iodoundecane C 11 H 22 BrI
28 Table S4. List of identified molecules with GC-MS from Eagle Ford neutral aliquot extracted with chloroform. Pk R.T. A[Tot] Compound name Qual. CAS # Mw Molecular Formula (min) (%) (%) Ammonia NH Methyl-1-butene C 5 H Trichloromethane CHCl Hydrochloric Acid HCl Hydrochloric Acid HCl (Pentyloxy)-hexane C 11 H 24 O Pentacosane C 25 H Tricosane C 23 H Triacontane C 30 H Pentacosane C 25 H Octacosane C 28 H Dotriacontane C 32 H Pentatriacontane C 35 H Tetradecane C 14 H Methyl-7-oxabicyclo[4.1.0]heptane C 7 H 12 O (1-Ethylpropyl)-heneicosane C 26 H 54
29 Triacontane C 30 H Nonacosane C 29 H Fluorododecane C 12 H 25 F Butyl-1-octanol C 12 H 26 O Pentadecane C 15 H ,2,2-Trifluorotetradecyl ester acetic acid C 16 H 29 F 3 O ,2,3,3,4,4,4-Heptafluoroundecyl ester butanoic C 15 H 23 F 7 O 2 acid Pentatriacontene C 35 H Pentacosane C 25 H Tricosane C 23 H Eicosane C 20 H Dotriacontane C 32 H Fluorododecane C 12 H 25 F Pentacosane C 25 H Tricosane C 23 H Eicosane C 20 H Dotriacontanol C 32 H 66 O Tritetracontane C 43 H 88
30 Pentadecen-1-ol C 15 H 30 O (3-Methyl-2-furanyl)-2-propanone C 8 H 10 O Heptadecane C 27 H ,6,10-Trimethyldodecane C 15 H Ethyl-1-decanol C 12 H 26 O Dotriacontane C 32 H Triacontane C 30 H Pentadecen-1-ol C 15 H 30 O Tetratetracontane C 44 H Tritetracontane C 43 H Triacontane C 30 H Hexatriacontane C 36 H Hexatriacontane C 36 H Hexatriacontane C 36 H Tetratetracontane C 44 H Triacontane C 30 H Dotriacontane C 32 H Hexatriacontane C 36 H Nonacosane C 29 H 60
31 ,2,3,3-Tetramethylhexane C 10 H Hexadecane C 16 H 34
32 Table S5. List of identified molecules with GC-MS from Eagle Ford (TX) acid aliquot extracted with chloroform. Peak R.T. (min) A[Tot] (%) Compound Q CAS # M w Molecular formula (%) Ammonia NH Methyl-2-pentene C 6 H Methyl-2-butene C 5 H Trichloromethane CHCl ,2,3,3-Tetramethylhexane C 10 H Pentyloxyhexane C 11 H 24 O Pentatriacontane C 35 H Dodecane C 12 H (Pentyloxy)-hexane C 11 H 24 O (1-Ethylpropyl)-heneicosane C 26 H Heneicosane C 21 H Docosane C 22 H Tricosane C 23 H Nonadecane C 19 H Tridecane C 13 H Eicosane C 20 H 42
33 ,6-Dimethylheptane C 9 H Tetradecane C 14 H ,4-Dimethylundecane C 13 H Methyltridecane C 14 H Tetratetracontane C 44 H Methyldodecane C 13 H Octacosane C 28 H Triacontane C 30 H Methyltridecane C 14 H Hexatriacontane C 36 H Nonacosane C 29 H Chloroheptacosane C 27 H 55 Cl Methylnonadecane C 20 H Dotriacontane C 32 H Dotriacontane C 32 H Pentatriacontane C 35 H Hexatriacontane C 36 H Triacontane C 30 H Tetratetracontane C 44 H 90
34 Hexatriacontane C 36 H Tetradecane C 14 H (Cyclohexylmethyl)-4-methylcyclohexane C 14 H Cyclotetradecane C 14 H Methyltetradecane C 15 H Bromooctadecane C 18 H 37 Br Bromohexadecane C 16 H 33 Br Bromopentadecane C 15 H 31 Br Bromooctadecane C 18 H 37 Br Octahydro-4a-methyl-2(1H)-naphthalenone C 11 H 18 O Pentadecane C 15 H Hexyl-1-decanol C 16 H 34 O ,5-dimethyl-7-Oxabicyclo[4.1.0]heptane C 8 H 14 O (2-Methylpropyl)-cyclohexane C 10 H methyl-2-(1-methylethyl)-cyclohexanol C 10 H 20 O ,8,10-Pentadecatriene C 15 H ,54-Dibromotetrapentacontane C 54 H 108 Br Hexadecane C 16 H (1-Butylheptyl)-undecane C 17 H 34
35 (1-Butylheptyl)-octadecane C 18 H 37 Br Methyl-3-(1-methylethyl)-cyclopentane C 9 H Methylpentatriacontane C 36 H ,54-Dibromotetrapentacontane C 54 H 108 Br Hexadecahydropyrene C 16 H Heptadecane C 27 H ,54-Dibromotetrapentacontane C 54 H 108 Br ,5-Dimethyl-7-oxabicyclo[4.1.0]heptane C 8 H 14 O Chlorohexadecane C 16 H 33 Cl (1-Propylnonyl)-cyclohexane C 18 H ,12-Dibromododecane C 12 H 24 Br Tritetracontane C 43 H Tetratetracontane C 44 H Hexatriacontane C 36 H Octadecane C 18 H ,54-Dibromotetrapentacontane C 54 H 108 Br Nonadecane C 19 H 40
36 Table S6. List of identified molecules with GC-MS from Barnett (NM) neutral aliquot extracted with chloroform. Peak R.T. A[Tot] Library/ID Q CAS # M w Molecular formula (min) (%) (%) Hydroxyacetonitrile C 2 H 3 NO ,1-Dimethylcyclopropane C 5 H Hexane C 6 H Trichloromethane CHCl α-2-propen-1-yl-benzenemethanol C 10 H 12 O ,3-Dimethylcyclopentane C 7 H cis-1,2-dimethylcyclopentane C 7 H ,3-Dimethylcyclopentane C 7 H Methylcyclohexane C 7 H ,2,4-Trimethylcyclopentane C 8 H Methyl-1-heptene C 8 H Methylheptane C 8 H Methylbenzene C 7 H ,3-Dimethylcyclohexane C 8 H cis-1-ethyl-2-methyl-cyclopentane C 8 H Octene C 8 H 16
37 ,6-Dimethylheptane C 9 H Ethylcyclohexane C 8 H ,1,3-Trimethylcyclohexane C 9 H cis-1,2-dimethylcyclopentane C 7 H ,2,4-Trimethylcyclohexane C 9 H Methyloctane C 9 H Ethylbenzene C 8 H ,2-Dimethylbenzene C 8 H Ethyl-3-methylcyclohexane C 9 H Nonane C 9 H Octahydro-2-methylpentalene C 9 H Propylcyclohexane C 9 H Decene C 10 H (E)-3-Heptene C 7 H Decene C 10 H Methylnonane C 10 H Ethyl-2-methylbenzene C 9 H Ethyl-2-methylbenzene C 9 H ,2,3-Trimethylbenzene C 9 H 12
38 ,3,5-Trimethylbenzene C 9 H Propyl-3-heptene C 10 H ,3,5-Trimethylbenzene C 9 H ,2,3-Trimethylbenzene C 9 H Decane C 10 H Methyldecane C 11 H Ethyl-2-methylbenzene C 9 H Propylcyclopentane C 8 H Ethyl-1,1,3-trimethylcyclohexane C 11 H Methyl-1-dodecanol C 13 H 28 O Methyl-3-propylbenzene C 10 H Methyltetradecane C 15 H Methyldecane C 11 H Methyldecane C 11 H Methyldecane C 11 H Pentylcyclohexane C 11 H Undecane C 11 H Decahydro-1-methyl-2-methylenenaphthalene C 12 H Decahydro-2-methyl-naphthalene, C 11 H 20
39 ,2,4,5-Tetramethylbenzene C 10 H Methyl-4-(1-methylethyl)-benzene C 10 H ,4-Dimethyl-2-(1-methylethenyl) C 10 H 18 O cyclopentanone ,4-dimethyl-2-(1-methylethenyl)-benzene C 10 H Methylundecane C 12 H Decahydro-2,3-dimethylnaphthalene C 12 H Dodecane C 12 H ,6-Dimethylundecane C 13 H ,6-Dimethylundecane C 13 H ,3-Dimethyldecane C 12 H Pentatriacontene C 35 H Methyltridecane C 14 H Tridecane C 13 H Methylnaphthalene C 11 H Cyclotridecane C 13 H ,2,3,4-Tetrahydro-1,5,7-trimethylnaphthalene C 13 H ,5,24-Trimethyltetracontane C 43 H Decahydro-2,3-dimethylnaphthalene C 12 H 22
40 ,6,10-Trimethyldodecane C 15 H ,6,10,14-Tetramethylhexadecane C 20 H Decahydro-2,3-dimethylnaphthalene C 12 H Tetradecane C 14 H Undecane C 11 H ,1,3-Trimethylcyclopentane C 8 H ,5-Dimethylnaphthalene C 12 H ,4-Dimethylnaphthalene C 12 H ,7-Dimethylnaphthalene C 12 H Methyleicosane C 21 H ,6,11-Trimethyldodecane C 15 H Nonadecane C 19 H Tritetracontane C 43 H Pentadecane C 15 H Hexacosanol C 26 H 54 O ,6,7-Trimethylnaphthalene C 13 H ,4,6-Trimethylnaphthalene C 13 H ,3,6-Trimethylnaphthalene C 13 H ,8-Dimethyldecane C 12 H 26
41 ,4,5-Trimethylnaphthalene C 13 H ,6,7-Trimethylnaphthalene C 13 H ,3,6-Trimethylnaphthalene C 13 H Hexadecane C 16 H Tridecane C 13 H ,2,3,4-Tetramethylnaphthalene C 14 H ,6,10-Trimethylpentadecane C 18 H Methyl-3-dodecen-1-ol C 13 H 26 O Heptadecane C 27 H ,6,10,14-Tetramethylpentadecane C 19 H Tetradecane C 14 H Hentetracontanol C 41 H 84 O Tetradecane C 14 H ,7-Dimethyl-7-octenal C 10 H 18 O ,1,3-Trimethylcyclopentane C 8 H Tetradecane C 14 H Octadecane C 18 H ,6,10,14-Tetramethylhexadecane C 20 H Methylhexadecanal C 17 H 34 O
42 ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane ,6,10-Trimethylundecanoic acid C 14 H 28 O Pentadecane C 15 H Methyltetradecane C 15 H Nonadecane C 19 H Nonadecene C 19 H Methylphenanthrene C 15 H Methyltetradecane C 15 H Methyltetradecane C 15 H ,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ol C 15 H 14 O Methyltetradecane C 15 H Methyl-3-dodecen-1-ol C 13 H 26 O Eicosane C 20 H Octadecene C 18 H Hexadecene C 16 H Octadecane C 18 H Octadecanethiol C 18 H 38 S Octadecane C 18 H 38
43 Heneicosane C 21 H Octadecanethiol C 18 H 38 S Hexadecane C 16 H Octadecanethiol C 18 H 38 S Hexadecane C 16 H Docosane C 22 H Tertadecen-1-ol acetate C 16 H 30 O Methyl-7-octadecene C 19 H Tetradecyloxirane C 16 H 32 O Heneicosane C 21 H Eicosane C 20 H Dodecene C 12 H Dodecene C 12 H Tricosene C 23 H Methyldocosane C 23 H Pentyl-2-propylcyclopentane C 13 H Docosane C 22 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane
44 Tetracosane C 24 H Decyloxirane C 12 H 24 O Cyclotetracosane C 24 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane Tricosane C 23 H Tetracosane C 24 H ,7,11-Trimethyl-4-(1-methylethyl) C 20 H 40 cyclotetradecane Tricosane C 23 H Pentacosane C 25 H Tetracosane C 24 H ,2-Diisooctyloate-1,2-benzenedicarboxylic acid C 24 H 38 O ,2-bis(2-Ethylhexyl)oate-1, C 24 H 38 O 4 benzenedicarboxylic acid Hexacosane C 26 H (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-binaphthalene]-5,5',8,8'-tetrone Hexacosane C 26 H 54
45 Tricosene C 23 H (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-binaphthalene]-5,5',8,8'-tetrone Acetate-11,13-dimethyl-12-tetradecen-1-ol C 18 H 34 O Heptacosane C 27 H Chlorooctadecane C 18 H 37 Cl Hexacosane C 26 H (Z)- 9-Methyl-4-undecene C 12 H ,2-Dioxide-6-dodecyl-1,2-oxathiane C 16 H 32 O 3 S Hexacosane C 26 H Butyl 2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid Butyl-2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid ,2-Didecyloate-1,2-benzenedicarboxylic acid C 28 H 46 O Butyl 2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid Butyl 2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid
46 Butyl-2-(8-methylnonyl)oate-1, C 22 H 34 O 4 benzenedicarboxylic acid Docosanethiol C 22 H 46 S (-)-1',4-Dihydroxy-7'-methoxy-2,3'-dimethyl C 23 H 16 O 7 [1,2'-Binaphthalene]-5,5',8,8'-tetrone Nonahexacontanoic acid C 69 H 138 O ,54-Dibromotetrapentacontane C 54 H 108 Br cis-4-ethyl-5-octyl-2,2-bis(trifluoromethyl)-1, C 15 H 24 F 6 O 2 dioxolane
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